WO2000068282A1 - Conditioning/styling terpolymers - Google Patents
Conditioning/styling terpolymers Download PDFInfo
- Publication number
- WO2000068282A1 WO2000068282A1 PCT/US2000/009065 US0009065W WO0068282A1 WO 2000068282 A1 WO2000068282 A1 WO 2000068282A1 US 0009065 W US0009065 W US 0009065W WO 0068282 A1 WO0068282 A1 WO 0068282A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- terpolymer
- alkyl
- dmapma
- terpolymer according
- terpolymers
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—Block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
- C08F220/606—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen and containing other heteroatoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Definitions
- This invention relates to polymers for use in hair and skin care compositions, and, more particularly, to conditioning and styling terpolymers having advantageous low tackiness and high humidity resistance.
- Copolymers of VP and DMAPMA have been used extensively as active components of hair and skin compositions . While these copolymers are generally suitable polymers for such products as conditioners and shampoos , it is desired to provide new polymers having improved performance characteristics in these and other personal care products .
- terpolymers of the invention comprises the following X, Y, and Z monomers, having the formulas given belo :
- Z is a quatemized derivative of an acrylic acid
- P is O or NR 2
- R l r R 2 , R 3 , R are independently H or C 1 -C 5 alkyl
- R 5 is a C 2 -C ⁇ 6 alkylene
- R 6 is C9-C2 4 alkyl
- M is a halide , tosylate or phosphate anion
- wt% of Z 0.25 to 50, preferably 1-30.
- the terpolymers of the invention are hydrophobically-modified cationic polymers having long alkyl-chains therein.
- a typical terpolymer thus has the following formulas :
- monomer Z is prepared by tosylating DMAPMA as follows :
- X is vinyl pyrrolidone
- Y is dimethylaminopropyl methacrylamide
- Z is a Ci 2 -C 18 alkyl quatemized derivative of an acrylic acid
- X is about 60-90 wt% , Y is about 5-30 wt% and Z is about 1-30 wt% ; Z is C 12 alkyl quatemized monomer; the weight average molecular weight of the terpolymer is 200,000 to 2,000,000; preferably 400,000 to 800,000; it is water soluble or water dispersible; and forms a clear humidity resistant, hydrophobic film when cast upon a support surface; which is surface active and hydrolytically stable; and is a homogeneous terpolymer.
- Cosmetic compositions of advantageous properties including about 0.1 to 10% by weight of the terpolymer can be prepared conveniently in this invention.
- the homogeneous terpolymers of the invention are made according to the method described by Kou-Chang Liu et al . in U.S. Patent 5,626,836.
- EXAMPLE 1 The preparation of (dodecyldimethyl methacryloimidopropyl ammonium tosylate) .
- [DMAPMA-C ⁇ 6 Ts] A mixture of 360 g of dodecyl tosylate and 200 g of DMAPMA were slowly heated up to 70°C without a solvent. Stirring was continued at 70°C for 2 hours. Then the reaction was cooled to room temperature and solidified product was further used in polymerization without purification .
- EXAMPLE 2 Terpolymer of VP/DMAPMA/DMAPMAA-C ⁇ 2 Ts Quat
- N-Vinylpyrrolidone (VP) (280 g) and deionized water (1400 g) are charged into a 2-liter resin pot equipped with a gas inlet, liquid inlet, a thermometer, and a condenser.
- the pH of the solution is adjusted to about 7.5 with KOH.
- a stream of nitrogen is introduced which bubbles through the solution during the reaction .
- the solution is gradually heated to 65°C for Lupersol® 11 catalyzed reaction, or to 78 °C for a Vazo® 67 initiated process.
- DMAPMA (17.5 g) and DMAPMAA-C ⁇ 2 Ts quat (52.5 g) are added continuously and uniformly into the pot with vigorous stirring for 4 hours so that the relative concentrations of the monomeric VP, DMAPMA, and DMAPMAA-C 12 TS quat monomer remain practically constant throughout the reaction at predetermined levels .
- Lupersol® 11 t-butylperoxy pivalate in mineral spirits
- the rate of the addition of the catalyst is such that 2 ml of Lupersol is completely delivered in 4 hours .
- the solution is held for an additional 3 hours at 68°C (or 78°C for Vazo 67 initiator) .
- the product is an aqueous solution of a homogeneous terpolymer of VP, DMAPMA and a DMAPMAA-C 12 Ts quat has a predetermined composition indicative of the relative amounts of each monomer used in the process and is substantially free of any residual homopolymer or copolymer .
- the yield of the terpolymer product is substantially quantitative.
- NaEDTA Ethylenediaminetetraacetic acid disodium salt dihydrate; Aldrich
- Aculyn 46 modified polyethylene glycol , enzymatically modified starch; Rohm & Haas
- the terpolymers of the invention have excellent wet combing, excellent dry feel and softness , and excellent wet feel .
- a styling lotion formulation was prepared in aqueous solution using 1% by weight of the terpolymer of Example 1 and 0.1% preservative.
- EXAMPLE 21 STYLING MOUSSE
- a concentrate is prepared by dissolving 1 g of the terpolymer of Example 1, 0.1 g of preservative and 98.9 g of deionized water.
- a styling mousse formation is prepared by mixing 70 g of the concentrate and 30 of hydrocarbon propellant in an aerosol can provided with a mousse dispenser.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00921731A EP1194460A4 (en) | 1999-05-07 | 2000-04-05 | Conditioning/styling terpolymers |
AU42008/00A AU767677B2 (en) | 1999-05-07 | 2000-04-05 | Conditioning/styling terpolymers |
KR1020017014153A KR100681630B1 (en) | 1999-05-07 | 2000-04-05 | Conditioning/styling terpolymers |
JP2000616253A JP4999230B2 (en) | 1999-05-07 | 2000-04-05 | Terpolymers for conditioning / styling |
CA2372457A CA2372457C (en) | 1999-05-07 | 2000-04-05 | Conditioning/styling terpolymers |
BRPI0010360-8A BR0010360B1 (en) | 1999-05-07 | 2000-04-05 | terpolymers for conditioning / modeling and cosmetic makeup. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/307,211 | 1999-05-07 | ||
US09/307,211 US6207778B1 (en) | 1999-05-07 | 1999-05-07 | Conditioning/styling terpolymers |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000068282A1 true WO2000068282A1 (en) | 2000-11-16 |
Family
ID=23188737
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/009065 WO2000068282A1 (en) | 1999-05-07 | 2000-04-05 | Conditioning/styling terpolymers |
Country Status (9)
Country | Link |
---|---|
US (1) | US6207778B1 (en) |
EP (1) | EP1194460A4 (en) |
JP (1) | JP4999230B2 (en) |
KR (1) | KR100681630B1 (en) |
CN (1) | CN1147510C (en) |
AU (1) | AU767677B2 (en) |
BR (1) | BR0010360B1 (en) |
CA (1) | CA2372457C (en) |
WO (1) | WO2000068282A1 (en) |
Cited By (125)
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WO2002058647A1 (en) * | 2001-01-26 | 2002-08-01 | L'oreal | Oxidation dyeing composition for keratin fibres comprising a cationic poly(vinyllactam) |
WO2002058660A1 (en) * | 2001-01-26 | 2002-08-01 | L'oreal | Oxidising composition for the treatment of keratin comprising a cationic poly(vinyllactam) |
WO2002058646A1 (en) * | 2001-01-26 | 2002-08-01 | L'oreal | Composition for treating keratinous materials comprising a cationic poly(alkyl) vinyllactam polymer and a protecting or conditioning agent |
WO2002058648A1 (en) * | 2001-01-26 | 2002-08-01 | L'oreal | Composition for direct dyeing of keratinous fibres comprising a poly(vinyllactam) |
WO2002058661A1 (en) * | 2001-01-26 | 2002-08-01 | L'oreal | Reducing composition for treating keratinous materials comprising a cationic poly(vinyllactam) |
WO2002058649A1 (en) * | 2001-01-26 | 2002-08-01 | L'oreal | Cosmetic composition comprising a fixing polymer and a cationic poly(vinyllactam) |
DE10160992A1 (en) * | 2001-12-12 | 2003-06-18 | Beiersdorf Ag | Hair fixer with anionic and / or amphoteric film polymer |
EP1319388A2 (en) * | 2001-12-12 | 2003-06-18 | Beiersdorf AG | Hair fixing composition with non-ionic film-forming polymer |
WO2003053381A1 (en) * | 2001-12-11 | 2003-07-03 | Basf Aktiengesellschaft | Cosmetic agent containing at least one copolymer having n-vinyllactam units |
US6602303B2 (en) | 2000-08-11 | 2003-08-05 | L'oreal S.A. | Composition for the oxidation dyeing of keratinous fibers comprising at least one oxidation dye and at least one cationic amphiphilic polymer, and dyeing methods |
EP1319390A3 (en) * | 2001-12-12 | 2003-12-17 | Beiersdorf AG | Composition for fixing the hair with a cationic compound |
JP2004149539A (en) * | 2002-10-21 | 2004-05-27 | L'oreal Sa | Oxidation dyeing composition for keratin fiber comprising cationic poly(vinyllactam) and at least one 10-14c fatty acid, oxydation dyeing process, and device |
EP1634575A1 (en) | 2004-09-13 | 2006-03-15 | L'oreal | Composition comprising at least one carbocyanine, process of treating keratinic fibres, kit and use of said composition |
EP1652554A1 (en) | 2004-09-13 | 2006-05-03 | L'oreal | Composition comprising at least one carboycanine, process of treating keratinic fibres, kit and use of said composition |
EP1652553A1 (en) | 2004-09-13 | 2006-05-03 | L'oreal | Composition comprising at least one carbocyanine, process of treating keratinic fibres, kit and use of said composition |
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Also Published As
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EP1194460A4 (en) | 2003-01-02 |
CA2372457A1 (en) | 2000-11-16 |
EP1194460A1 (en) | 2002-04-10 |
JP2002544299A (en) | 2002-12-24 |
US6207778B1 (en) | 2001-03-27 |
AU767677B2 (en) | 2003-11-20 |
CA2372457C (en) | 2010-06-22 |
BR0010360B1 (en) | 2011-02-22 |
CN1350558A (en) | 2002-05-22 |
KR20010113912A (en) | 2001-12-28 |
AU4200800A (en) | 2000-11-21 |
BR0010360A (en) | 2002-02-13 |
KR100681630B1 (en) | 2007-02-09 |
CN1147510C (en) | 2004-04-28 |
JP4999230B2 (en) | 2012-08-15 |
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